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Merck
CN

73328

Sigma-Aldrich

三甲基氰硅烷

technical, ≥95% (GC)

别名:

TMSCN, 氰化三甲基硅烷

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About This Item

线性分子式:
(CH3)3SiCN
CAS号:
分子量:
99.21
Beilstein:
1737612
EC 号:
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22

等级

technical

质量水平

方案

≥95% (GC)

表单

liquid

折射率

n20/D 1.392 (lit.)

沸点

114-117 °C (lit.)

mp

8-11 °C (lit.)

密度

0.793 g/mL at 20 °C (lit.)

SMILES字符串

C[Si](C)(C)C#N

InChI

1S/C4H9NSi/c1-6(2,3)4-5/h1-3H3

InChI key

LEIMLDGFXIOXMT-UHFFFAOYSA-N

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应用

Trimethylsilyl cyanide (TMSCN) can be used as a reagent in the:
  • Cyanosilylation of carbonyl compounds using various catalysts.
  • Synthesis of α-aminonitriles by one-pot, three-component Strecker reaction of ketones with various amines using Brønsted acid catalyst.
  • Cyanation of aryl halides using palladium-complex as a catalyst.

警示用语:

Danger

危险分类

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Flam. Liq. 2

补充剂危害

储存分类代码

3 - Flammable liquids

WGK

WGK 3

闪点(°F)

33.8 °F - closed cup

闪点(°C)

1 °C - closed cup

个人防护装备

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

法规信息

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分析证书(COA)

Lot/Batch Number

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Indium tribromide: a highly effective catalyst for the addition of trimethylsilyl cyanide to ?-hetero-substituted ketones
Bandini M, et al.
Tetrahedron Letters, 42(16), 3041-3043 (2001)
Asymmetric addition of trimethylsilyl cyanide to ketones catalyzed by Al (salen)/triphenylphosphine oxide
Kim SS and Kwak Ju M
Tetrahedron, 62(1), 49-53 (2006)
A convenient and efficient procedure for the palladium-catalyzed cyanation of aryl halides using trimethylsilylcyanide
Sundermeier M, et al.
Journal of Organometallic Chemistry, 684(1-2), 50-55 (2003)
Alessandro Sacchetti et al.
Organic & biomolecular chemistry, 9(15), 5515-5522 (2011-06-21)
We investigated the Strecker-type reaction of isatin derived chiral ketimines with TMSCN in the presence of a Lewis acid. The desired α-amino nitriles have been obtained in good yields with moderate diastereoselectivity. Further elaboration of the cyanide group allowed the
Ying-Chuan Qin et al.
Organic letters, 7(12), 2381-2383 (2005-06-04)
[reaction: see text] An efficient one-step synthesis of the optically active bifunctional BINOL ligand (S)-3 has been developed. It was found that (S)-3 in combination with Me2AlCl is a highly enantioselective catalyst for the addition of TMSCN to aliphatic aldehydes

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